What the Fuck is Serena Wearing

Serena van der Woodsen wears some ridiculous, inappropriate shit. Our goal is to document these outfits.
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What is more appropriate for a “state dinner” (please, Gossip Girl) than a dress that is cut down to the navel and slit up to the vag? It’s also backless because, you know, necessary. (Also: WE’RE BACK! I tried to document Serena’s terrible outfits in season 2 during the hiatus but then I remembered that season 2 was pretty boring. So.)

What is more appropriate for a “state dinner” (please, Gossip Girl) than a dress that is cut down to the navel and slit up to the vag? It’s also backless because, you know, necessary.

(Also: WE’RE BACK! I tried to document Serena’s terrible outfits in season 2 during the hiatus but then I remembered that season 2 was pretty boring. So.)

In Serena’s world, that strip of fabric passes for a skirt and is totally acceptable for Thanksgiving dinner.

In Serena’s world, that strip of fabric passes for a skirt and is totally acceptable for Thanksgiving dinner.

It’s so hard to tell rebellious-because-of-mean-stepfathers Serena from the normal, everyday, “what’s wrong with having my tits hanging out during math class (not that I actually go to school ever)” Serena.

It’s so hard to tell rebellious-because-of-mean-stepfathers Serena from the normal, everyday, “what’s wrong with having my tits hanging out during math class (not that I actually go to school ever)” Serena.

Serena apparently didn’t feel secure enough after wearing a shirt cut down to her navel to meet with the Dean of Admissions. She’s certainly displaying some assets.

Serena apparently didn’t feel secure enough after wearing a shirt cut down to her navel to meet with the Dean of Admissions. She’s certainly displaying some assets.

Here’s another Special Guest Appearance by Vanessa. Those crazy vaguely ethnic bohemians and their shiny, shiny jackets!

Here’s another Special Guest Appearance by Vanessa. Those crazy vaguely ethnic bohemians and their shiny, shiny jackets!

It’s no wonder the Yale Dean of Admissions is smiling so widely. That’s a deep, deep v on Serena’s shirt, which is, by the way, totally appropriate for meeting with the Dean of Admissions of Yale.

It’s no wonder the Yale Dean of Admissions is smiling so widely. That’s a deep, deep v on Serena’s shirt, which is, by the way, totally appropriate for meeting with the Dean of Admissions of Yale.

On the one hand, every woman wants to show off her assets when meeting her ex’s new fling. On the other, sometimes subtlety is underrated. Serena doesn’t seem to know what that word means.

On the one hand, every woman wants to show off her assets when meeting her ex’s new fling. On the other, sometimes subtlety is underrated. Serena doesn’t seem to know what that word means.

Special Guest Edition: Vanessa Vanessa had far more…interesting clothing in the first season of Gossip Girl. This dress was apparently made by Lil J, budding fashion designer, and it’s very difficult to figure out which aspect of it is the most appalling. The color? The tulle petticoat? The sleeves? The general shape? It’s a riddle wrapped up in a mystery inside an enigma - just like Soviet Russia.

Special Guest Edition: Vanessa

Vanessa had far more…interesting clothing in the first season of Gossip Girl. This dress was apparently made by Lil J, budding fashion designer, and it’s very difficult to figure out which aspect of it is the most appalling. The color? The tulle petticoat? The sleeves? The general shape? It’s a riddle wrapped up in a mystery inside an enigma - just like Soviet Russia.

One must wonder about Serena’s thought process for dressing for her mother’s many weddings. Does she base the amount of cleavage shown on how much she disapproves of her mother’s new husband? She certainly seems to dislike Bart Bass enough to show copious amounts of sideboob, as well as a little bit of underboob.

One must wonder about Serena’s thought process for dressing for her mother’s many weddings. Does she base the amount of cleavage shown on how much she disapproves of her mother’s new husband? She certainly seems to dislike Bart Bass enough to show copious amounts of sideboob, as well as a little bit of underboob.

Would the Chuck of today wear a shirt with a crowns and bare knuckles print? Would the Chuck of today wear matching blue sweatbands? Possibly.

Would the Chuck of today wear a shirt with a crowns and bare knuckles print? Would the Chuck of today wear matching blue sweatbands?

Possibly.

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